The former England striker and his companion were seen chatting while they sat in the front of his £150,000 Range Rover Evoque.
Defoe was all smiles as he arrived and began chatting to the mystery woman
The pair met up in the car park of posh golf club Brocket Hall in Hertfordshire
Jermain and the mystery lady initially spoke in the front seat of his Range Rover
Then, the pair switched ends as they joined each other on the back seat in a golf club car park.
Earlier, the woman had arrived in a separate car to which she returned to after her meeting with ex-Spurs star Defoe in his vehicle.
An onlooker in the car park, used by the public who can turn up to play golf as non-members at posh Brocket Hall in Hertfordshire, said: "He was in the driver's seat of his car on his own.
"Then she turned up in her car, parked and walked over to his, and got in the front next to him.
"They seemed to chat for a bit before she got out of the front and got back into the car on the back seat.
"I didn't see him get out but then I noticed he was also sitting on the back seat next to her.
"I've no idea what they were doing but they were on the back seat together for around 15 to 20 minutes.
"At one point a jacket appeared to have been tied between the two head-rests of the front seats. It was all very odd."
Defoe, 41, has been in a relationship with influencer Alisha Lemay, sharing a holiday in the Caribbean at the beginning of this year and were spotted on a date in London in July.
He has also been liking her Instagram content, featuring her in sexy dresses and swimwear, as recently as last month.
They hit a rocky patch last September when Defoe, now a coach and TV pundit, got together with wedding planner Paige Mallabourn-Edmondson, 29, who moved into his home.
But they reunited after he split from Paige.
Defoe split with wife Donna Tierney, 40, just seven months after they tied the knot in 2022 in a £200,000 wedding featured in OK! magazine.
The Sun on Sunday revealed Defoe, whose other clubs included West Ham, Sunderland and Glasgow giants Rangers, had been messaging a nurse begging for sex with her and to join him in his Range Rover.
The pair were seen chatting in the backseat where they spent 20 minutes together
Former footballer Jermain has had an on-off relationship with influencer Alisha Lemay
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